Triphenylphosphine → HCID 86597574, compound

Participants

Reaction Steps

Diisopropylazodicarboxylate (921 mg, 4.56 mmol) was added portionwise, at room temperature, to a stirred suspension of 4-chloro-6-methoxyquinazolin-7-ol (800 mg, 3.80 mmol), 3-[4-(2-fluoroethyl)piperazin-1-yl]propan-1-ol (794 mg, 4.18 mmol) and triphenylphosphine (1.4 g, 5.34 mmol) in THF (20 ml). The reaction was stirred 1 hr. before adding triphenylphosphine (1.4 g), di-tert-butylazodicarboxylate (1.05 g, 4.56 mmol) and dichloromethane (10 ml). The reaction was stirred for a further 1 hr. then evaporated and purified by column chromatography on silica using increasing concentrations of methanol in dichloromethane as eluent then on alumina (neutral) using 10% methanol in dichloromethane as eluent to give 4chloro-7-{3-[4-(2-fluoroethyl)piperazin-1-yl]propoxy}-6-methoxyquinazoline (696 mg, 48%) as a colourless solid; NMR Spectrum:(CDCl3) 2.13 (quintet, 2H), 2.55 (m, 10H), 2.67 & 2.76 (dt, 2), 4.06 (s, 3H), 4.30 (t, 2H), 4.53 & 4.64 (dt, 2H), 7.36 (s, 1H), 7.38 (s, 1H), 8.86 (s, 1H).

Provenance & Evidence